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Studies towards the synthesis of hyperireflexolide A.

ABSTRACT: The first approach to hyperireflexolide A, based on the synthesis of ?-lactone-fused cyclopentane 5, a functionalized key intermediate, is presented. Compound 5 is involved in hydrolysis, ?-allylation at C-8 and ?-methylation at C-10 stereoselectively from the convex face. Then it is subjected to cross metathesis to give ?,?-unsaturated ketone 11 as precursor in the total synthesis of hyperireflexolide A.

SUBMITTER: Rao GHM

PROVIDER: S-EPMC6122383 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Studies towards the synthesis of hyperireflexolide A.

Rao G Hari Mangeswara GHM

Beilstein journal of organic chemistry 20180813

The first approach to hyperireflexolide A, based on the synthesis of γ-lactone-fused cyclopentane 5, a functionalized key intermediate, is presented. Compound 5 is involved in hydrolysis, α-allylation at C-8 and α-methylation at C-10 stereoselectively from the convex face. Then it is subjected to cross metathesis to give α,β-unsaturated ketone 11 as precursor in the total synthesis of hyperireflexolide A. ...[more]

PMID: 30202464

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